Receipt of one’s first pay cheque equals a liberty unrestrained. This, at last, is money earned and carries with it no obligation other than that it should be spent foolishly, without guilt, and with indecent haste. My first cheque was for the princely amount of £66.30 as reward for a music paper interview with a long-forgotten quasi-Goth band. One hour after the cheque had cleared, all funds had been squandered on pop records, vodka and cheese. In time, I’d come to realise that a pay cheque was required to cover all of life’s essentials and that man cannot survive on good tunes, hard liquor and cheddar alone. At least while the illusion lasted, I was as free as a mountain bird.

My first bespoke suit was bought from a shop in Brighton’s North Lanes in 1998. Walking home I realised I felt taller, bolder and sharper-looking than I’d ever felt before. Those feelings redoubled when a tall blonde woman wearing a Nirvana t-shirt wolf-whistled me in the street. Some moments have ‘freedom’ written right through them. She turned out to be a great kisser too.

Learning to swim is something most of us do shortly after we learn to walk. It took me that little bit longer. In 2001, still a non-swimmer at the age of 40, I came perilously close to drowning off the coast of Honduras. A few months later, I took my first swimming lessons. On my fourth lesson, I was moving in the water without that sinking feeling and my joy was unconfined. Learning to do anything useful for the first time frees the soul.

The Birmingham Six were returned to some kind of freedom on the afternoon of 14 March 1991. For close to 6,000 days and nights, they had languished behind bars for crimes (the 1974 Birmingham pub bombings in which 21 people died) they’d had no involvement in. The television images remain profoundly indelible. Six men (Paddy Hill, John Walker, Hugh Callaghan, Richard McIlkenny, Gerry Hunter and William Power) emerge angry and exultant from the Old Bailey, greeted by tight scrums of family, friends and supporters. The noise builds to a rousing climax, people dance, pigeons scatter in all directions. Far above them, on the building’s dome, the gilded figure of Justice stares away into the distance, already in grim possession of the knowledge that a nation’s shame will never be laid to rest. As all this plays out, the value of freedom regained is being measured against those years of freedom criminally snatched away.

“Ali KO’d Foreman with a lightning-fast left and right combination, he was fighting his own freedom struggle.”

Potato Head Blues might not be the greatest recording Louis Armstrong ever made (that honour surely goes to West End Blues). But there’s an argument to be made for Potato Head Blues being the great man’s most groundbreaking work. Recorded in May 1927 with his Hot Seven ensemble, it’s significant mainly for Armstrong’s cornet solo following the banjo break. A feat of thrilling improvisation, this is the moment when Louis first swings, really swings, elevates jazz to an art form, and holds the world in thrall. The seeds of everything truly revolutionary that followed in rhythm & blues, rock’n’roll and soul music is embodied in this 44-second solo. It’s the sound of freedom made exquisite. Small wonder that in Manhattan Woody Allen  lists it among the things that make his life worth living.

The Great Escape climaxes with Steve McQueen’s ‘Cooler King’ Hilts leading the German army on a merry chase through the countryside. His remaining moments of freedom are fast counting down. But he’s relishing and cherishing every last one. No matter that McQueen was replaced by a stuntman for that iconic 60-foot motorcycle jump over the Austrian-Swiss fence, we willingly suspend disbelief with every bank holiday viewing and root for Hilts as he revs up and rides towards his fate. In those audacious few minutes before he becomes entangled in the barbed wire, he looks like the freest man ever to draw breath.

Jack Kerouac’s On The Road is one of those novels that is less important as an enduringly great work of art and far more important for the seismic impact it provides on first reading. A spontaneous hymn to restless self-discovery, On The Road no longer engages me the way it did when I first read it at the age of 16. But that first reading inspired me to pack my bag, stick out my thumb and wait for the lift that would whisk me away from small town Wales in hot pursuit of a second shot at life. Sal Paradise and Dean Moriarty dared me to be free and cheered me on all the way to London where dreams could finally be realised.

Steve Fossett had achieved everything he had set out to achieve by the age of 40. His ambition had been to make a lot of money in the American financial services industry. Fossett made so much money that, at times, he couldn’t say for sure whether he was a multi-millionaire or a billionaire. But, crucially, he’d made so much money that he’d become bored with accumulating wealth. As he entered his fifth decade, Fossett decided to devote the rest of his life to adventure. So he embarked on a mission to set world records in some of the world’s most demanding endurance events. Between the mid-Eighties and the present, he set 116 records in five different sports and is probably best known for being the first man to fly solo non-stop around the world in a balloon, which he did in 2002. Fossett personifies the universal truth that it’s never too late in life to taste freedom by stopping what you are doing and venturing into something new and potentially dangerous.

The Berlin Wall was part of a 103-mile-long fortification encircling West Berlin and, for 28 years, remained the most potent symbol of Cold War division and Communist tyranny. On the beautifully uncontrolled night of 9 November 1989, the wall came down. And what a night. Hours after, the Communist authorities announced the removal of travel restrictions to democratic West Berlin, they converged on the crossing points in their hundreds of thousands — drinking, dancing, hacking away at the fortifications in defiant jubilation. As gaps in the wall appeared, so the spontaneous counter-flow of bodies between east and west began.

A country was reborn, the Cold War was nearing its end, East Germany’s Communist regime was finished and would soon be followed by the fall of Communist governments throughout Europe. Some great force was let through the Berlin air that night. The force of freedom.

The Rumble In The Jungle lays fair claim to be the greatest heavyweight boxing match of all time. By the time of this historic 1974 bout, Muhammad Ali was already a legend. Indeed, his legend would have been assured purely on the strength of the punches he landed outside the ring. Through the turbulent Sixties, Ali emerged as a radical symbol of dissent, his courageous opposition to the Vietnam war and support for human rights around the world making him a key figure in the forging of a new global consciousness.

“Fossett personifies the universal truth that it’s never too late in life to taste freedom.”

Yet by the time the 32-year-old came to fight the 26-year-old George Foreman in Zaire, he was already being dismissed as a man whose powers were sharply on the wane. When, in the eighth round of the fight, Ali KO’d Foreman with a lightning-fast left and right combination to regain a second world title, he was fighting his own freedom struggle, one demonstrating his primacy as an athlete of supreme skill, effortless grace and indomitable spirit.

A helicopter ride across the Grand Canyon is the fairground thrill to top them all. Strap yourself in and prepare to be pumped with wonder. The ride towards the canyon, taking in the Sonora desert, the snowcapped Bradshaw Mountain range and the ponderosa pine forests is spectacular enough. But nothing prepares you for that first glimpse of the earth’s largest gorge, 280 miles long and 11 miles wide. It’s a transformative sight, one that will guarantee you’ll never feel blasé about the power of nature ever again. When that chopper glides over the Grand Canyon, the sense of freedom you feel is a pure intimate connection with geological time.

The Palio of Siena lasts just 75 seconds but contains the drama and passion of centuries. Since 1650, the 17 wards (contrade) of this magnificent Tuscan city have been competing in a twice-yearly horse race that provides a spectacle like no other. To describe the Palio simply as a horse race would be misleading though. The race itself provides the thrilling finale to weeks of sumptuous feasts and colourful festivities. Behind the scenes, the normal rules of horse-racing do not apply.

Doping, bribery and physical attacks on rival jockeys are not only permitted but actually encouraged. A similar lawlessness applies to the race, which takes place in the majestic Piazza del Campo. Jockeys are issued with whips made out of bull phalluses and, during their three headlong laps around the square, are expected to thrash both jockeys and horses to gain advantage. Broken bones and lashings of blood are par for the course. But you’d be mistaken in concluding that the Palio amounts to little more that an excuse for ritualised violence. It’s nothing less than an ecstatic celebration of Sienese culture, values and identity; Italian passion at its most gloriously free.